L-Lysine monohydrochloride
Basic Molecular and Structural Characteristics
- Molecular weight: 182.65 g/mol (free L-lysine: 146.19 g/mol; the hydrochloride moiety increases the molecular weight and modulates solubility/ stability).
- Chirality: L-configuration (the natural and biologically active isomer; D-lysine is non-bioactive and rarely used in industrial applications). The chiral center is at the α-carbon atom (C2), with the amino group (−NH3+) in the L-configuration (S-configuration in CIP nomenclature).
- Ionic nature: At physiological pH (7.35–7.45) and aqueous solution, it exists as a zwitterion with a hydrochloride counterion: the α-amino group (−NH2) and ε-amino group (−NH2) are protonated to NH3+, the carboxyl group (−COOH) is deprotonated to COO−, and the Cl− ion remains free in solution to maintain electrical neutrality.
- Structural formula: H2N−(CH2)4−CH(NH3+)−COO−⋅Cl− (zwitterionic form in water); the neutral molecular formula for the solid salt is NH2−(CH2)4−CH(NH2)−COOH⋅HCl.
- Isoelectric point (pI): ~9.74 (calculated from its three dissociation constants: pKa1 (α-COOH) = 2.18, pKa2 (α-NH3+) = 8.95, pKa3 (ε-NH3+) = 10.53). At pH < 9.74, it carries a net positive charge in solution— a key feature for its interaction with anionic biomolecules (e.g., proteins, nucleic acids).
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